N‐Heterocyclic‐Carbene‐Catalysed Diastereoselective Vinylogous Mukaiyama/Michael Reaction of 2‐(Trimethylsilyloxy)furan and Enones. Issue 12 (15th October 2015)

• Record Type: Journal Article
• Authors: Wang, Ying; Du, Guang‐Fen; Xing, Fen; Huang, Kuo‐Wei; Dai, Bin; He, Lin
• Is Part Of: Asian journal of organic chemistry. Volume 4:Issue 12(2015:Dec.)
• Page Start: 1362
• Page End: 1365
• Publication Date: 2015-10-15
• Subjects: butenolides -- enones -- N-heterocyclic carbenes -- 2-(trimethylsilyloxy)furan -- vinylogous Mukaiyama/Michael reaction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201500348
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: N‐heterocyclic carbenes have been utilised as highly efficient nucleophilic organocatalysts to mediate vinylogous Mukaiyama/Michael reactions of 2‐(trimethylsilyloxy)furan with enones to afford γ‐substituted butenolides in 44–99 % yield with 3:1–32:1 diastereoselectivity. Abstract : M and M : N‐heterocyclic carbenes act as highly efficient organocatalysts to mediate the vinylogous Mukaiyama/Michael reaction of 2‐(trimethylsilyloxy)furan and enones to afford γ‐substituted butenolides in 44–99 % yield with 3:1–32:1 anti/syn selectivity.